Szmuszkovicz U.S. Pat. No. 3,510,492 discloses and claims some 2-anilino- and 2-anilinomethylcycloalkylamines which are useful as antidiabetic drugs in that they can be administered in low dosages for reducing blood sugar. However, that patent does not teach or suggest the compounds of this invention or the uses which have been found for these compounds. This U.S. Pat. No. 3,510,492 also discloses but does not claim compounds of the formula ##STR2## as compounds of structure XV in column 4 thereof, where n is 1 to 4, R.sub.1 and R.sub.2 are hydrogen, C.sub.1 to C.sub.4 -alkyl, benzyl or R.sub.1 and R.sub.2 together with the nitrogen to which they are bonded denote a cyclic amino group of the formula ##STR3## containing 5 to 9 nuclear atoms, and R.sub.4 and R.sub.5 are hydrogen, C.sub.1 to C.sub.4 -alkyl, C.sub.1 to C.sub.4 -alkoxy, hydroxy, halogen or trifluoromethyl.
Rynbrandt et al., U.S. Pat. No. 3,647,804 discloses some 2-amino-cycloalkane-1-carboxamides and diamines which are said to be useful pharmaceutical drugs because of their hypoglycemic, sedative, and anti-inflammatory activities, but that patent does not suggest the amide types of this invention or the pharmacological activities claimed for the compounds of this invention.
F. Winternitz, et al., in Bull. Soc. Chim., France, 382 (1956) discloses the compound N-(2-dimethylaminocyclohexyl benzamide for the purpose of obtaining a solid derivative of a liquid diamino compound but that article contains no reference to biological data.
N. J. Harper et al., in J. Chem. Soc., 4280 (1964) discloses compounds of the formula ##STR4## where X is hydrogen, m-fluoro or p-chloro. The stereochemistry of those compounds was not indicated with certainty. In a hot plate test, using pethidine (meperidine) as standard (activity=1) the analgesic activity of these amide compounds where X was p-chloro was 0.22. In the electroshock test it was 34 percent as active as diphenylhydantoin, but all of those compounds lacked activity in the antiamphetamine and antireserpine tests.
R. T. Brittain et al. in the Brit. J. Pharm., 49, page 158 p. (1973) disclose some 1-amino-1-benzoamidomethylcyclohexane analgesic compounds of the formulae: ##STR5## wherein X is hydrogen, 4-F, 3,4-di-Cl, 2-Cl, 3-Cl or 4-Cl. ##STR6## where X is 4-fluoro, 3,4-dichloro or 2-chloro; and ##STR7## where X is hydrogen or 3,4-dichloro, but those compounds are not 1,2-cyclohexyldiamine derivatives, as are the compounds of this invention.
Those skilled in the analgesic art continue to search for new and useful compounds.